81840-57-5Relevant academic research and scientific papers
Concise and efficient total synthesis of oxyphyllacinol, yakuchione-A and yakuchione-B
Deng, Yu,Kurtz, Nicole C.,Shi, Xiang,Sun, Yue,Wu, Xian,Xue, Mingxing
, (2022/02/14)
A concise and efficient method for the large-scale total synthesis of oxyphyllacinol (1) has been achieved in six steps with an overall yield of 46%. Simultaneously, yakuchione-A (11) was obtained in a satisfactory yield (52%) during the process. By employing a Weinreb amide (6) as the key masonry block, yakuchione-B (13) was also constructed in a great overall yield (56%) and high purity. To overcome the challenges regarding the practical scale, high purity, and reproducibility, the synthetic route that was processed takes advantage of available materials, conventional reactions, and convenient purification methods without using column chromatography.
Suppression of inducible nitric oxide synthase expression by yakuchinones and their analogues
Lee, Hwa Jin,Kim, Ji Sun,Yoon, Joung Wha,Kim, Hee-Doo,Ryu, Jae-Ha
, p. 377 - 379 (2007/10/03)
Analogues of yakuchinones were synthesized as inhibitors of nitric oxide production in lipopolysaccharideactivated macrophage cell line, RAW 264.7 cells. We prepared stronger inhibitors than the original natural molecules, yakuchinones A and B reported from Alpinia oxyphylla. From the limited structural activity relation study of analogues, we concluded that the optimal length of linker between two aryl groups and the presence of enone moiety in the linker were identified as essential for the activity. The IC50 value of the most potent structure was 0.92 μM. The active analogues suppressed the expression of inducible nitric oxide synthase protein and mRNA.
Synthesis of diarylheptanoids and assessment of their pungency
Itokawa,Aiyama,Ikuta
, p. 2491 - 2496 (2007/10/02)
With the aim of correlating pungency with substituent groups on one benzene ring, various analogues of yakuchinones were synthesized by means of the Claisen-Schmidt reaction. Their pungencies were assessed by direct comparison of the threshold concentrations obtained in taste experiments. The presence of a phenolic hydroxyl group was indispensable for high pungency, while that of a 1,2-double bond of the heptanone part tended to decrease the pungency.
